Hydrogen Bromide → 16-Bromohexadecanoic acid

Participants

Reaction Steps

A 2 liter three neck round bottom flask, equipped with a mechanical stirrer, reflux condenser and nitrogen inlet, was charged with 177 g (0.63 moles) of 16-hydroxy hexadecanoic acid 1. To this vessel were added 1000 mL (5 moles) of 30% hydrogen bromide in acetic acid and 310 mL of concentrated sulfuric acid. The system was equipped with sequential traps containing a sodium hydroxide pellet trap, a 25% aqueous sodium hydroxide solution trap and a saturated sodium carbonate trap. The reaction stirred overnight at room temperature before it was heated to reflux for six hours. The reaction mixture was cooled, poured over ice water and the precipitated solid was filtered under vacuum. After drying under high vacuum, 196 g of 16-bromohexadecanoic acid was obtained.

Provenance & Evidence